|
|||||
|
|
Synthesis of orthogonally protected l-threo-β-ethoxyasparagine |
|
| Authors: | Jan Spengler Marta Pelay Judit Tulla-Puche Fernando Albericio |
| Institution: | 1. Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028, Barcelona, Spain 2. CIBER-BBN, Networking Centre on Bioengineering Biomaterials and Nanomedicine, Barcelona Science Park, University of Barcelona, Baldiri Reixac 10, 08028, Barcelona, Spain 3. Department of Organic Chemistry, University of Barcelona, Martí i Franqués 1-11, 08028, Barcelona, Spain |
| Abstract: | Orthogonally protected l-threo-β-ethoxyasparagine (Fmoc-EtOAsn(Trt)-OH, 1) was synthesized from diethyl (2S,3S)-2-azido-3-hydroxysuccinate 2 in eight steps as a building block for solid-phase peptide synthesis. The starting material is easily available in multi-gram scale from d-diethyltartrate. The transformation steps reported here are robust and scalable. Thus, a significant amount of 1 (1.8 g) was obtained in 21% overall yield. The synthesis reported is also expected to be useful for the preparation of other O-substituted l-threo-β-hydroxyasparagine derivatives. |
| Keywords: | |
| 本文献已被 SpringerLink 等数据库收录！ | |